Indian Forest Service (Mains), Chemistry optional · 2021 · Paper II
Q7(b). Ireland–Claisen rearrangement of an allylic acetate
Question
Predict the reaction of the drawn cis cyclohexenyl diacetate with LDA at −78 °C followed by TBDMSCl, and give the mechanism. [structure given in the paper]
Model answer
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CoversIreland–Claisen rearrangementsilyl ketene acetal[3,3]-sigmatropic rearrangementLDATBDMSCl
All parts of Question 7
- 7(a)(i) A beta-chloroamine and sulfonyl chloride5 marks
- 7(a)(ii) Hydration followed by oxidation5 marks
- 7(b) Ireland–Claisen rearrangement of an allylic acetate10 marks
- 7(c)(i) Solvolysis of a tertiary allylic bromide5 marks
- 7(c)(ii) Ring expansion of vinylcyclobutane5 marks
- 7(d) Stability of triarylmethyl radicals5 marks
- 7(e) State-dependent diene chemistry and photo-Fries rearrangement5 marks